JPS6051178A - N-(2-nitrophenyl)-5-aminopyrimidine derivative, manufacture and vermicide - Google Patents

Abstract

The invention discloses novel N-(2-nitrophenyl)-5-aminopyrimidine derivatives of the general formula <IMAGE> (I) wherein R1 and R2 are each independently NO2 or CF3, or one of R1 and R2 is hydrogen, R3 is hydrogen or halogen, R4 is hydrogen or the -C(O)R' group, in which R' is C1-C4alkyl which is unsubstituted or substituted by halogen, C1-C3alkoxy or C1-C3alkylthio, R5, R6 and R7 are each independently hydrogen, halogen, nitro, cyano, thiocyano, mercapto, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6alkoxy which is substituted by halogen, nitro, cyano, C1-C3alkoxy, C1-C3alkylthio and/or N(C1-C4alkyl)2; or are C3-C6cycloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6alkylthio, C3-C6alkenylthio, C1-C6alkylsulfonyl, C1-C6alkylsulfoxyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl or the N(C1-C4alkyl)2 group, and R5 may additionally be a phenyl or benzyl group which is unsubstituted or substituted by one to three identical or different members selected from halogen, nitro, cyano, C1-C4alkyl, C1-C3haloalkyl, N-(C1-C3alkyl) 2, and/or C1-C3alkoxy. The preparation of these compounds and their use in agriculture are also disclosed.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel N-(2-nitrophenyl)-5-aminopyrimidine/conductor represented by the following formula 1. The invention further relates to the preparation of these compounds and to agrochemical compositions containing at least one of these novel compounds as active ingredient. The present invention also relates to the preparation of such compositions and the use of novel compounds or compositions for controlling harmful microorganisms, preferably phytopathogenic fungi and phytopathogenic bacteria.

Specifically, the present invention relates to the general formula 1 [wherein R7 and R2 independently represent NO, a group, or a CF3 group, or one of R and R2 represents a hydrogen atom, and R3 is a hydrogen atom or represents a halogen atom, R4 is a hydrogen atom or a -C(OIR' group (in the group, R' is unsubstituted or substituted with a halogen atom, an alkoxy group having 1 to 3 carbon atoms, or an alkylthio group having 1 to 3 carbon atoms) represents an alkyl group having 1 to 4 carbon atoms, and R5, R6 and R7 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyan group, a thiocyano group 1. a mercapto group, a mercapto group, a carbon atom number; 1 to 6 alkyl group, C1 to C6 haloalkyl group, C1 to C6 alkyl group
an alkoxy group, or a halogen atom, a nitro group, a cyano group, an alkoxy group having 1 to 30 carbon atoms, an alkylthio group having 1 to 3 carbon atoms, and/or N (alkyl having 1 to 4 carbon atoms)! represents a C1-C6 alkoxy group substituted by a group, or a C3-C6 cycloalkoxy group, a C5-C6 alkenyloxy group, a C3-C6 alkenyloxy group; an alkynyloxy group, an alkylthio group having 1 to 6 carbon atoms, an alkenylthio group having 3 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms,
Alkylsulfoxyl group having 1 to 6 carbon atoms, alkenyl group having 3 to 6 carbon atoms, haloalkenyl group having 3 to 6 carbon atoms, alkynyl group having 3fx to 6 carbon atoms, and alkynyl group having 3 to 6 carbon atoms; Represents a haloalkynyl group or 2 N (alkyl having 1 to 4 carbon atoms) group, and R6 is further unsubstituted or a halogen atom, nitro group, cyan group, alkyl group having 1 to 4 carbon atoms, 1 carbon atom substituted with 1 to 3 same or different groups selected from 2 to 3 haloalkyl groups, 2 N-(alkyl having 1 to 3 carbon atoms), and/or alkoxy groups having 1 to 3 carbon atoms; It may also be a phenyl or benzyl group. ] This relates to a compound represented by:

Depending on the number of carbon atoms defined, an alkyl group itself or as part of another substituent such as an alkoxy group, a haloalkyl group, a haloalkoxy group, etc. represents, for example, a straight-chain or branched group: methyl group , ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc. and their isomers such as isopropyl group, isobutyl group, tert-butyl group, impentyl group, etc.

Throughout this specification, a substituent affixed with I'halo means that the substituent may be mono- or perhalogenated.Halogen atom and halo are 7-atom, chlorine atom, bromine atom, or iodine atom. Therefore, a haloalkyl group means a mono- to perhalogenated alkyl group such as CHC
l,, CTl2F, CCl3, CH, CI, CHF
,,CH2CH2Br.

Represents C, C15, CH2Br 5CHBrCI, etc.
And preferably represents CF3. Examples of alkenyl groups include 1-propenyl group, allyl group, 1-butenyl group, 2-
Represents a chain containing a butenyl or 3-butenyl group and several double bonds.

Depending on the defined number of carbon atoms, the cycloalkyl group represents, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, etc. Examples of the alkynyl group include a 2-propynyl group, a propargyl group, a 1-butenyl group, a 2-butenyl group, and a propargyl group is preferred.

The compounds of formula 1 are oily, resinous or predominantly crystalline solids that are stable under normal conditions and have very useful microbicidal properties.

These can be used prophylactically and therapeutically in agriculture or related fields, for example to control phytopathogenic pests such as fungi. The compounds of formula 1 exhibit excellent fungicidal properties and a broad spectrum of activity when applied over a wide range of concentrations, and are problem-free in use.

The following groups of compounds are preferred for their pronounced microbicidal, in particular bactericidal, properties: Group Ia: In formula 1, RI represents a nitro group, R2 represents a trifluoromethyl group, R3 represents a chlorine atom, R
4 is a hydrogen atom or -C(0)-R' (in the group, R' is unsubstituted or a carbon substituted with a halogen atom, an alkoxy group having 1 to 3 carbon atoms, or an alkylthio group having 1 to 3 carbon atoms) represents an alkyl group having 1 to 4 atoms.], and R5 is a hydrogen atom, a halogen atom, a cyano group, a thiocyano group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or a carbon an alkoxy group having 1 to 6 atoms, a haloalkoxy group having 1 to 3 carbon atoms, an alkylthio-(alkoxy having 1 to 3 carbon atoms) group having 1 to 3 carbon atoms,
C1-C5 alkylthio, C1-C3 alkoxy substituted by two N (C1-C2 alkyl) groups, or C3-C4 alkenyloxy; radical, C3-C4alkenylthio, C1-C6
alkylsulfonyl group, C1-C3 alkylsulfoxyl group, NlC1-C3 alkyl)2 group or unsubstituted or fluorine atom, chlorine atom,
Bromine atom, nitro group, cyano group, methoxy group, C1-C4 alkyl group, dimethylamino group or C
Represents a phenyl or benzyl group substituted with 1 to 3 same or different groups selected from F3, and R6 and Ry 75' independently of each other are a hydrogen atom, a hydrogen atom, a cyano group, a thiocyano group , C1-C6 alkyl group, C1-C5/-roalkyl group, C1-6 alkoxy group, halogen atom, nitro group, C1-C5 alkoxy group, carbon an alkylthio group having 1 to 3 atoms or an alkoxy group having 1 to 3 carbon atoms substituted with 2 groups of N (alkyl having 1 to 4 carbon atoms), or an alkylthio group having 1 to 40 carbon atoms; Alkylsulfonyl group having 1 to 3 atoms, alkylsulfoxyl group having 1 to 6 carbon atoms, alkenyloxy group having 3 to 4 carbon atoms, alkenylthio group having 3 to 4 carbon atoms, 6 to 4 carbon atoms an alkynyloxy group, a C5 -C4 alkynylthio group or N (C1 -C3 alkyl)2
A compound representing a group.

fl'1ilb: In the formula (■), RI represents a di)o group, R2 represents a trifluoromethyl group, R3 represents a hydrogen atom, and R
4 is a hydrogen atom or -C(OJ R' group (in the group, R' is an unsubstituted or carbon atom substituted with a halogen atom, an alkoxy group having 1 to 6 carbon atoms, or an alkylthio group having 1 to 6 carbon atoms) represents an alkyl group having numbers 1 to 4), and R5 is a hydrogen atom, a halogen atom, a cyan group, a thiocyano group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms,
C1-C6 alkoxy group, C1-C3 haloalcokyne group, C1-C3 alkylthio- (C1-C3 alkoxy) group, C1-C6 alkylthio group , a C1-C3 alkoxy group substituted with two N-(C1-C2 alkyl) groups, or a C6-C40 alkenyloxy group, a C3-C4 alkyl group; Alkenylthio group, C1-C3 alkylsulfonyl group, C1-C3 alkylsulfoxyl group, N (C1-C5 alkyl)! group or unsubstituted or 1 to 6 same or different selected from fluorine atom, chlorine atom, bromine atom, nitro group, cyano group, methoxy group, alkyl group having 1 to 4 carbon atoms, dimethylamino group or CF3 and R6 and R7 are each independently a hydrogen atom, a halogen atom, a cyano group, a thiocyano group, a C1-176 argyl group, a C1-C3 a haloalkyl group, a C1-C6 alkoxy group,
C1-C6 alkyl substituted with halogen, nitro, C1-C3 alkoxy, C1-C3 alkylthio or 2 N (C1-C4 alkyl) groups represents an alkoxy group or an alkylthio group having 1 to 4 carbon atoms,
C1-C5 alkylsulfonyl group, C1-C3 alkylsulfoxyl group, C3-C4 alkenyloxy group, C3-C4 alkenylthio group, C3-C4 alkenylthio group 4 a/l
/ Oxy group, C5-C4 alkynylthio group, or N (C1-C3 alkyl)
Compounds representing two foundations.

Group ■c: Expression! In 1C, RI represents a trifluoromethyl group, R2 represents a nitro group, R3 represents a hydrogen atom,
R4 is a hydrogen atom or -c (0) R' group (in the group, R'
is unsubstituted or )・rogen atom, carbon number 1 to 3
represents an alkyl group having 1 to 4 carbon atoms substituted with an alkoxy group or an alkylthio group having 1 to 3 carbon atoms. ), R5 is a hydrogen atom, a halogen atom, a cyano group, a thiocyano group, an alkyl group having 1 to 6 carbon atoms, or a C 1 to 6 alkyl group.
C1-C6 no-roalkyl group, C1-C6 alkoxy group, C1-C3 haloalkoxy group, C1-C30 alkylthio-(C1-C3 alkoxy) group, carbon Number of atoms: 1 to 3
represents an alkylthio group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms substituted by 2 groups of N (alkyl having 1 to 2 carbon atoms), or an alkenyloxy group having 3 to 4 carbon atoms, having 3 carbon atoms; an alkenylthio group having 1 to 4 carbon atoms, an alkylsulfonyl group having 1 to 3 carbon atoms, an alkylsulfoxyl group having 1 to 5 carbon atoms,
2 groups of N (alkyl having 1 to 3 carbon atoms), or unsubstituted fluorine atom, chlorine atom, 'bromine atom, nitro group, cyano group, methoxy group, alkyl group having 1 to 4 carbon atoms, dimethylamino represents a phenyl or benzyl group substituted with one to three same or different groups selected from R6 or CF3, and R6
and R7 are each independently a hydrogen atom, a halogen atom, a cyano group, a thiocyano group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a halogen a nitro group, a C1-C6 alkoxy group, a C1-C3 alkylthio group or a C1-C3 alkyl group substituted with two N (C1-C4 alkyl) groups; represents an alkoxy group or an alkylthio group having 1 to 4 carbon atoms, 1 to 3 carbon atoms;
alkylsulfonyl group, C1-C6 alkylsulfoxyl group, C3-C4 alkenyloxy group, C3-C4 alkenylthio group, C6-4 alkynyl group, txy base, charcoal
A compound representing an alkynylthio group having 3 to 4 atoms or 2 N (alkyl having 1 to 3 carbon atoms) groups.

Group 1d: Compounds of formula I in which R1 represents a hydrogen atom, U represents a hydrogen atom, R2 represents a CF3 or NO, a crow represents a hydrogen atom, and other substituents have the meanings given in Group 1a.

Group ■f In formula I, R1 is N9. or CF, R
Compounds in which 2 represents a hydrogen atom, R3 represents a hydrogen atom, and the other substituents have the meanings given for group 1a.

Group 1g: In formula I, R1 represents NO, or CF3, and R
1 represents NO or CF, R3 represents a hydrogen atom or a halogen atom, and R4 represents a hydrogen atom or -C(
In the OIR′ group C group, R′ is unsubstituted or a halogen atom,
It represents a C1-C4 alkyl group substituted by a C1-C3 alkoxy group or a C1-C6 alkylthio group. ), R
5.R6 and R7 are each independently a hydrogen atom, a hydrogen atom, a nitro group, a cyan group, a thiocyano group, a mercapto group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, Alkoxy group having 1 to 6 carbon atoms, norogen atom, nitro group, cyano group,
C1-C3 alkoxy group, C1-C3 alkylthio group and/or C1-C6 alkoxy group substituted by C1-C4 alkyl22 group or C3 -C6 cycloalkoxy, C5
-6 alkenyloxy group, having 3 -6 carbon atoms
an alkynyloxy group, an alkylthio group having 1 to 6 carbon atoms, an alkenylthio group having 5 to 6 carbon atoms,
C1-C6 alkylsulfonyl group, carbon U
1 to 6 alkylsulfoxyl groups or 2 N (alkyl having 1 to 40 carbon atoms) groups, and R5 is further unsubstituted, or -rogen atom, nitro group, -cyano group, carbon Alkyl group having 1 to 4 atoms, no-roalkyl group having 1 to 3 carbon atoms, N
(Alkyl having 1 to 3 carbon atoms) is a phenyl or benzyl group substituted with 1 to 6 same or different groups selected from 2 groups and/or alkoxy groups having 1 to 3 carbon atoms; A compound that can.

Within the scope of the above group, compounds in which the substituent R4 represents a hydrogen atom are particularly preferred.

Examples of particularly preferred individual compounds are: N-(5'-chloro-27,6/-dinitro-4'-
trifluoromethylphenyl)-5-amino-4-chloro-6-methoxypyrimidine (compound 1.1), N-(3'-chloro-2-6'-dinitro-4'-trifluoromethylphenyl)- 5-amino-4゜6-cyphthylthiopyrimidine (compound 1.2), N-13'-
-chloro-2',6'-dinitro-4'-trifluoromethylphenyl)-5-amino-4゜6-trifluoroethoxypyrimidine (compound 1.6), N-+ 3'-chloro-2' , 6'-dinitro-4'
-trifluoromethylphenyl)-5-minnow 4゜6
-dichloropyrimidine (compound t4), N-(3
'-Chloro-2', 6'-dinitro-47-trifluoromethylphenyl)-5-amino-4-chloro-6-
Methylmercaptovirigodine (compound 1.1841, N-(3'-chloro-2-6fusinitro-4'-trifluoromethylphenyl)-5-amino-4-chloro-
2-Methyl-6-methoxypyrimidine (compound 1.20
5), N-(5-chloroo-2', 6'-dinitoa-4'
-trifluoromethylphenyl)-5-amino-2-chloro-4-methoxypyrimidine (compound 1, 51 J, N-(3'-chloro-2', 6'-7 nitro 47-
trifluoromethylphenyl)-5-amino-2゜4-
Dichloropyrimidine (compound 1.491, N-(5'-
Chloro-2', 6'-7 nitro-4'-trifluoromethylphenyl)-5-ami/-2-chloro-4-allyloxyvirimine (compound 1.210), N − + 3'-chloro -2',6'-dinitro-4-hood trifluoromethylphenyl-5-amino-2-chloro-4-allylmercaptopyrimidine (compound 157
), N-(3'-chloro-2',6'-dinitro-4'-trifluoromethylphenyl)-5-chloro-2-chloro-4-propargyloxypyrimidine (compound 1,21
11, N-(3'-chloro-2;6'-dinitro-4'-trifluoromethylphenyl)-5-amino-4°6-dichloroo-2-methylpyrimidine (compound 1.96), N- (5'-chloro-2',6'-dinitro-4'-trifluoromethylphenyl)-5-amino-4°6-dichloro-2-phenylpyrimidine (compound 1,1251
, (2J, 6/-7 nitro-4'-trifluoromethylphenyl)-5-amino-4,6-')chloropyrimidine (compound 2.4), N-,2/,4/-dinitro-6' -trifluoromethylphenyl)-5-ami/-4,6-schifa apyrimidine (Compound 54), N-12', 4', 6'-trinitrophenyl)
-5-amino-4,6-dichloropyrimidine (compound Z
1), N −+ 2'-nitro-4'-trifluoromethylphenyl)-5-amino-4,6--2chlorohydrinomidine (compound 8.1) The compound represented by formula i is represented by the following formula (■) : (In the formula, Hal represents a halogen atom, preferably a chlorine atom or a bromine atom, and R, R, and R8 have the above meanings.) A compound represented by the following formula (in the formula, R6 , R6 and R7 have the above meanings.)
A compound represented by the following formula I': (wherein, RI% R2, R3, R5, R6 and R7 have the above-mentioned meanings) by reacting with a pyrimidine derivative represented by the following in the presence of a base σ) and converting the compound represented by the formula ■' into an N-acyl compound N-acylated with a reactive derivative of a carboxylic acid represented by the following formula ■: The process consists of obtaining a chemical derivative.

The following reaction conditions are advantageous for preparing compounds of formula 1 and/or formula I': N-alkylation reaction of (Il) and (till to obtain (1) and (11 and (IVI N)
-Acylation reactions occur with dehydrohalogenation.

, the reaction temperature for N-alkylation is -60°C to +150°C.
°C, preferably in the range of -50 °C to +30 °C, and the reaction temperature for N-acylation is 0 ° to 180 °C.
, preferably L< is in the range 0° to +150° C. or the boiling point of the solvent or solvent mixture.

It is advantageous to use acid acceptors or condensing agents in both reactions. Examples of suitable acid acceptors or condensing agents are organic and inorganic bases, such as tertiary amines: trialkylamines (trimethylamine, triethylamine, tripropylamine, etc.), pyridine and pyridine bases (4-dimethylaminopyridine, 4-pyrrolidylamino), etc. hyridine, etc.)
, alkali metal and alkaline earth metal oxides, hydroxides, carbonates and bicarbonates, and alkali metal acetates.

The reaction can be carried out in the presence of an inert solvent or diluent. Examples of suitable solvents and diluents are aliphatic and aromatic hydrocarbons examples, t habenzene, toluene, xylene, petroleum ether: halogenated hydrocarbons such as chlorobenzene, methylene chloride, ethylene chloride, chloroform, tetrachloride. Carbon, tetrachloroethylene: ethers and ethereal compounds such as dialkyl ethers (
(diethyl ether, diisopropyl ether, tert-butyl methyl ether, etc.), anisole, dioxane, tetrahydrofuran: Nitriles such as γcetonitrile and babionitrile: N, N-dialkylated amides such as dimethylformamide: dimethylsulfoxide:
Ketones such as acetone, diethyl ketone, methyl ethyl ketone: and mixtures of such solvents. In some cases, the acylating or alkylating agent itself may be used as a solvent. The presence of a catalyst such as dimethylformamide is advantageous.

(The reaction with Ill71llD can also be carried out in aqueous two-phase systems according to the generally known principle of phase transfer catalysis.

For example, the following solvents are suitable for the organic water-immiscible phase: aliphatic and aromatic hydrocarbons, such as evapentane, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, etc.: halogenated hydrocarbons, such as dichloromethane. , chloroform, carbon tetrachloride, ethylene dichloride, 1,2-dichloroethane, tetrachloroethylene, etc., or aliphatic ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, etc.

Examples of suitable phase transfer catalysts are: tetraalkylammonium halides, hydrogen sulphates or hydroxides such as tetraalkylammonium chloride, tetraalkylammonium bromide, tetrabutylammonium iodide, triethylbenzylammonium chloride or triethylbenzylammonium bromide, tetrapropylammonium chloride, tetrapropylammonium bromide, or tetrapropylammonium iodide. Phosphonium salts are also suitable phase transfer catalysts. The reaction temperature generally ranges from -50° to 130°C and may also be the boiling point of the solvent or solvent mixture.

Unless specified otherwise, one or more inert solvents or diluents may be present in the preparation of all starting materials, intermediates, and final products described herein. Examples of suitable inert solvents or diluents are: aliphatic and aromatic hydrocarbons such as benzene, toluene, xylene, petroleum ethers, halogenated hydrocarbons such as chlorobenzene, methylene chloride, ethylene chloride, chloroform, Carbon chloride, tetrachloroethylene; ethers and ethereal compounds such as dialkyl ethers (diethyl ether, improbyl ether, tertiary-
(methyl methyl ether, etc.), anisole, dioxane,
Tetrahydro7rane; nitriles such as acetonitrile,
N,N-dialkylated amides such as dimethylformamide; dimethyl sulfoxide; ketones such as acetone, diethyl ketone, methyl ethyl ketone; and mixtures of such solvents. It is often convenient to carry out the reaction, or some steps of the reaction, under an inert gas atmosphere and/or in an anhydrous solvent.

Suitable inert gases include nitrogen, helium, argon, and the like.

The starting materials of the formula (1) are generally known or can be prepared by methods known per se.

The pyrimidine represented by the formula ■ is a textbook on heterocyclic compounds (for example, pyrimidine).

J. Brown, The Pyrimidine I
Pyrimidines)") or can be prepared by methods analogous to those described therein.

The above-described manufacturing method, including all the partial steps, forms an important object of the invention.

Surprisingly, the inventors have discovered that the compounds of formula I have a fungicidal spectrum that is highly beneficial against phytopathogenic fungi and bacteria in practice. They have very advantageous curative, systemic and especially prophylactic properties and can be used to protect various cultivated plants. The compound represented by the formula ■ can be used to suppress or eradicate microorganisms that occur on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of various beneficial crops. At the same time, later growing parts of the plant are also protected from attack by phytopathogenic microorganisms and insects.

The compounds of Part 2 are effective as microbicides against phytopathogenic fungi belonging to the following classes: Deuteromycota [e.g.
m), Fusarium l, Septorial, Cercospora
pora) and Deuteromycota (Alternaria
l) Lentigo fungi [e.g. Hem1 Ieia]
IA's lentiginous fungi, Rhizoctonia (Rh1zocoto
nia), Puccinia l and, in particular, cystomycetes [e.g.
ria), Podosphaera
a), Erysiphe l, Monilinial fMonilinial, Unci
nula)).

Furthermore, the compounds of formula 1 have osmotic properties. They can also be used as seed dressings against fungal infections of seeds (fruits, tubers, grains) and plant cuttings and against phytopathogenic fungi occurring in the soil.

The invention therefore also relates to compositions for pest control, in particular fungicidal compositions, and methods for their use in agriculture or related fields.

Furthermore, the present invention also includes a method for preparing an agrochemical composition comprising homogeneously mixing the active ingredient with one or more compounds or compounds described herein. The invention furthermore relates to a method for treating plants by applying a compound of formula 1 or to a novel composition thereof.

Target crops to be protected within the scope of the invention are, for example, the following types of plants: cereals (wheat, barley, rye, oats, rice, sorghum and related crops), beets [sugar beets and fodder beets]. beet)), stone fruits, pears and soft fruits (apples, pears, plums, peaches, cherries, Dutch strawberries, rasberries and black berries), leguminous plants (broad beans, lentils, peas, soybeans), oil plants (brassica, curran, poppy, olive, sunflower, coconut, castor oil plant, cocoa beans, peanuts), cucumber plants (cucumber, pumpkin, melon), fiber plants (cotton, flax) , hemp, jute), species fruits (orange, melon, grapefruit, Chinese mandarin orange), vegetables (greens, lettuce, asparagus, cabbage, garlic, onion, tomato, paprika), Lauraceae (avocado, cinnamon, camphor) or corn, tobacco, nuts, coffee, sucrose, tea, vines, pumps, bananas and natural rubber, and ornamental plants (mixtures).

The compounds of formula I are usually applied in the form of compositions and can be applied simultaneously or sequentially with other compounds to the cultivated area or plants to be treated. These compounds may be fertilizers or micronutrient providers or other preparations that influence plant growth. They are also selective herbicides, insecticides, fungicides, bactericides, nematocides, molluscicides (mol lusicide).
or a mixture of several of these preparations;
If desired, they may also be used with other carriers, surfactants or application aids commonly used in the art of formulation. Suitable carriers and auxiliaries may be solid or liquid and correspond to the substances commonly used in compounding technology, such as natural or recycled mineral substances, solvents, dispersants,
It is a wetting agent, adhesive, binder or fertilizer.

A preferred method of application of the agrochemical composition containing the compound of formula I or at least one of the compounds described above is foliar application. The number and rate of application depends on the risk of infection by the corresponding pathogen (type of fungus).

However, the compounds of formula I can also be applied by impregnating the cultivated area with a liquid composition or by applying the compound to the soil in solid form, for example in the form of granules (
It can enter the plant through the soil (osmotic action) through the soil.

Compounds of formula 1 above may also be applied to seeds by applying a liquid formulation containing the compound of formula I to the seeds and slicing or coating them with a solid composition (coating). In special cases, further forms of application are also possible, for example weekly selective treatment of plant stems or buds.

The compounds of the formula I are used in neat form or preferably together with the auxiliaries customary in formulation technology and can therefore be used as emulsion concentrates, coating pastes, direct sprays or diluted aqueous solutions, diluted emulsions. , hydrating agents, water-soluble powders, powders,
The granules are incorporated in known manner and also, for example, by encapsulation with polymeric substances. Depending on the nature of the composition, the application methods such as spraying, atomizing, dusting, scattering or pouring are selected depending on the intended purpose and the prevailing circumstances. Advantageous rates of application are usually 50 F to 5 Kp of active ingredient (a, i, ) per hectare, preferably f-1100 g to 2 Kg s, i, /ha and most preferably 2
00pi to l5OOF a, i, /ha.

Formulations, e.g. compositions or formulations comprising a compound of formula I above (active ingredient) and, if appropriate, solid or liquid auxiliaries, are prepared in known manner, e.g. fillers e.g. solvents, solid carriers. and, if appropriate, the active ingredient together with surface-active compounds (surfactants) and/or
or by crushing.

Suitable solvents are: aromatic hydrocarbons, preferably fractions containing 8 to 12 carbon atoms, e.g. aliphatic hydrocarbons, alcohols, glycols and their ethers and esters, such as ethanol, ethylene glycol, etc.
monoethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide and evaporated vegetable oils such as nieboxylated coconut oil or soybean oil. , or water.

The solid carriers used, for example for powders and dispersants, are usually natural mineral fillers such as calcite, talc, kaolin, montmorillonite or attapulgite. It is also possible to add highly dispersed silicic acid or highly dispersed adsorbent polymers to improve the physical properties. Suitably granulated adsorptive carriers are of the porous type, for example pumice, crushed brick, sepiolite or bentonite, and suitable non-adsorptive carriers are materials such as calcite or sand. In addition, a large number of mineral or organic pre-granulated materials can be used, such as dolomite or pulverized plant residue, among others. Adjuvants which particularly advantageously aid the application, which sufficiently reduce the rate of application, may also be natural (animal or vegetable) or synthetic phospholipids of the cephalin and lecithin series, such as phosphatidylethanolamine. , phos-7 atidylserine, phosphatidylcholine, sphingomyelin, bosphatidylinintole, phosphatidylglycerol,
Phosphorlecithin, frasmalocenes or calciolibin, and these can be obtained, for example, from animal or plant cells, especially from brain, heart, liver, egg yolk, and even soybean. An example of a useful material form is a phosphatidylcholine mixture. Examples of synthetic phospholipids are dioctanoylphosphatylcholine and dipalmitoylphosphatylcholine.

Depending on the nature of the compound of formula I to be formulated, suitable surface-active compounds are anionic, cationic and/or nonionic surfactants with good emulsifying, dispersing and wetting properties. The term "surfactant" is also to be understood as including mixtures of surfactants.

Suitable nonionic surfactants include both water-soluble surfactants and water-soluble synthetic surface-active compounds.

Suitable soaps include higher fatty acids (10 to 22 carbon atoms).
), or unsubstituted or substituted ammonium salts, such as the sodium or potassium salts of oleic acid or stearic acid, or of natural fatty acid mixtures obtained, for example, from coconut oil or tallow oil. Also included are fatty acid methyltaurine salts.

However, so-called synthetic surfactants are more frequently used, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylaryl sulfonates.

Fat sulfonates or sulfates are usually alkali metal salts,
in the form of alkaline earth metal salts or unsubstituted or substituted ammonium salts and containing C 8 -C 22 alkyl groups (including the alkyl part of acyl groups): for example sodium or calcium salts of lignosulfonic acid or dodecyl Sodium or calcium salts of sulfate esters or sodium or calcium salts of fatty alcohol sulfate ester mixtures obtained from natural fatty acids.

These compounds also include sulfate esters of fatty alcohol/ethylene oxide adducts and salts of sulfonic acids.

The sulfonated benzimidazole derivatives preferably have 2 sulfonic acid groups and 1 having 8 to 22 carbon atoms.
Contains 3 fatty acid groups. Examples of alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, matahanaphthalenesulfonic acid/formaldehyde condensate. Corresponding phosphates are also suitable, for example the salts of the phosphoric esters of p-nonylphenol adducts with 4 to 14 moles of ethylene oxide.

The nonionic surfactants are preferably aliphatic or cycloaliphatic alcohols or polyglycol ether derivatives of saturated or unsaturated fatty acids and alkylphenols;
Its derivatives contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon part and 6 to 18 carbon atoms in the alkyl part of the alkylphenol.
Contains carbon atoms.

Other suitable nonionic surfactants are polyethylene oxide and polypropylene glycol, ethylene-diamino polypropylene glycol and 1 to 1 in the alkyl chain.
water-soluble adducts with alkyl polypropylene glycols having 0 carbon atoms;
0 ethylene glycol ether groups 10 [210
Contains 0 globylene glycol ether groups. The above compounds usually contain 1 to 5 per propylene glycol unit.
Contains ethylene glycol units.

Representative examples of nonionic surfactants are nonylphenol-polyethoxyethanol, castor oil polyglycol ether, polypropylene/polyethylene oxide adduct, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitan and polyoxyethylene rubitan trioleate are also suitable nonionic surfactants.

Notionic surfactants preferably contain at least one alkyl group having 8 to 22 carbon atoms as N-substituent, unsubstituted or halogenated lower alkyl group, benzyl group or lower hydroxyalkyl group as further substituent. It is a quaternary ammonium salt containing a base alloy. The salt is preferably in the form of a halide, methyl sulfate or ethyl sulfate, such as stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethyl ammonium bromide.

Surfactants commonly used in the pharmaceutical industry are described, for example, in the publications listed below.

Mc Cutcheo's Detergents and Emulsion Firers Annual
n's Detergents and Emulsi
fiersAnnual 1″+ MC Publishers, Ringwood (New Chassis,
1981: Helmut Starr (Helmut 5tache)
Written by Dr. L, [Surfactant] Ndobunoku (Ten5i
dTaschenbuch)”, Carl Hauser Publishers, Munich/
Vienna (Mffnchen/Wien) 1981
Year.

Agrochemical formulations usually contain from 0.1 to 99%, preferably from 11 to 95%, of a compound of formula I, from 1 to 99.9%, preferably from 99.8 to 5%, of a solid or liquid adjuvant, and a surfactant. It contains from 1 to 725%, preferably from 1 to 25%.

Although commercial products are preferably formulated as concentrates, consumers typically use dilute formulations.

The compositions may also contain other ingredients such as stabilizers, defoamers, viscosity regulators, binders, tackifiers and fertilizers or other active ingredients for special effects.

Such agricultural compositions also constitute an object of the present invention.

The present invention will be illustrated in more detail by the following examples, which are not intended to limit what is described herein. Parts and percentages are by weight.

Production Example Example P1: N −+ 3'-chloro-2;6'-dinitro-47-
Preparation of 5-amino-4-chloro-6-medoxypyrimidine (trifluoromethylphenyl)-5-amino-4-chloro-6-medoxypyrimidine N0II OCH3 5-amino-4-chloro-6-medoxypyrimidine 2
．． 84P (17.8 mol) Odimethyl sulfoxide 2
0a! Dissolves in +. While stirring, add 1,6-dichloro-2,6-sinitro 4 to dimethyl sulfoxide 15-.
-T! J Fluoromethyl Hensen/(&24p (20
, 5 mol) and dimethyl sulfoxide 1
Potassium tertiary phyllo to 5al) 2.509 +
20.5 mmol) is simultaneously warmed at 15°C. The dark red solution so obtained is stirred for 1 hour at 15° to 20° C., then poured into ice water, neutralized with acetic acid and extracted three times with chloroform. The extract is dried over sodium sulfate and the solvent is removed on a rotary evaporator to yield an oil at 7.9 F. This crude product was purified by chromatography through a column of silica gel to yield a crystalline product 5.
．． Get 19ri. 2 rrtl of toluene and 8r of cyclohexane! Recrystallization from a mixture of Ll gives 2.521 yellow crystals, melting point 114°-116°C.

Example P2 N-(3'-Chloro ~ 2L, 6Fuge Nitro 47
-drifluoro-a-methylphenyl)-5-amino-4゜6
- Preparation of dimethylpyrimidine NO2H3C5 1. 3-dichloro-2,6-sinitro 4-trifluoromethylbenzene Z32p (o, 24 mm!J mole) is dissolved in dimethyl sulfoxide 30-, then dimethyl sulfoxide 20- A solution of 3.75y (20 mmol) of 5-diminnow 4.6-cyphthylthiopyrimidine dissolved in .1 and a solution of 2.69F of potassium tert-butyrate dissolved in 20m of dimethyl sulfoxide were simultaneously cooled at 15°C. Add easily. The reaction solution is stirred for 15 hours at 20° C., then poured into ice-water, neutralized with acetic acid and extracted three times with chloroform. The extract is washed with water, dried over sodium sulfate and the chloroform removed to give a yellow oil 10.7F. The crude product was purified by chromatography through a column of silica gel, containing 2.04% of the starting 5-amino-4,6-di(methylmercapto)pyrimidine, and 5% of the hydrene 1- and cyclohexane.
A yellow product 2.8y was obtained which was recrystallized from RT and had a melting point of 146° to 147°C, compound 1.2:2.
．． Get 03y.

Example P3: N −+ 3'-riguchi-2', 6'-dinitro-4
'-trifluoromethylphenyl)-5-amino-41
Preparation of 6-ditrifluoroethoxypyrimidine 1.5-dichloro-2,6-sinitro 4-trifluoromethylbenzene (11 mol) dissolved in 20 m of dimethyl sulfoxide [5, then 5-amino in 15 m of dimethyl sulfoxide A solution containing 2.62F (9 mmol) of -4,6-dydolyfluoroethoxypyrimidine and a solution containing 2.475E (22 mmol) of potassium tert-butyrate in 15m dimethyl sulfoxide were simultaneously cooled to 15°C. Add. The dark red solution thus obtained is stirred for 3 hours at room temperature. Still contains the starting pyrimidine. Furthermore, 1゜3-dichloro-2,
6-sinitro 4-trifluoromethylbenzene 2-
Oy (6,9 IJ mol l) and potassium tert-butyrate (13,4 mmol) are added. Extraction and column chromatography give the yellow product 354y.

Recrystallized from toluene 1d and cyclohexane 9-,
Products with a melting point of 97° to 99°C2. get oay.

Lifluoromethylphenylcin-5-amino-4゜6-
Preparation of dichloropyrimidine According to the procedure of Example P3, 1.64 parts of 5-amino-4°6-dichloropyrimidine and 1,3-dichloro-2,6
-Sinitro 4-) IJ Fluoromethylbenzene 3.
05F was reacted in dimethyl sulfoxide in the presence of potassium tert-butyrate 167y (D) to give a melting point of 12
1.817 of pure product is obtained between 7° and 128°C.
High yields and pure products are obtained by using tetrahydrofuran as solvent instead of dimethyl sulfoxide in Examples P1 to P4 and by carrying out the reaction at a temperature range of -50°C to -30°C.

Example P5゜N -(3'-chloro-2',6'-dinitro-4'-
trifluoromethylphenyl)-5-amino-4゜6~
Dichloro-2-methylpyrimidine 1,5-dichloro-2,6-sinitro 4-trifluoromethylbenzene 6.71 g ((1022 mol) and 5-amino-4,6-dichloro-2-methylpyrimidine s, s6y ( 0,020 mol in 50 ml of tetrahydrofuran.The solution is cooled to -30°C and at this temperature a solution of 4.67 (0,041 mol) of potassium tert-butyrate in 50 ml of tetrahydrofuran is warmed.1 After an hour, at -50° to 0°C, the mixture is extracted with water and ethyl acetate while adding 10 WLl of acetic acid.The extract is dried over sodium sulfate and concentrated to give a crude product of 10.5 W Ll as an oil. The product is purified by chromatography through a column of silica gel using 3 parts of petroleum ether and 1 part of ethyl acetate. The solvent is removed on a rotary evaporator to give the product a3yf as a residue. Recrystallized from a mixture of toluene and cyclohexane, melting point 16
Yellow crystals from 4° to 136°C
9.2%).

The compounds of formula I below are prepared by methods analogous to those described in the examples above.

Formulation examples (all percentages are by weight) Compounds from Tables 1 to 9 25% 40% 50% Cyclohexanone-15
% 20% Xylene Mixture 65% 25% 20% Emulsions of the required concentration can be made by diluting such concentrates with water.

F2. Solution a) b) cl d1 Table 1 is not available! -7
Compound 9 80% 10% 5% 95% polyethylene glycol 400 - 70% --N-methyl-2-pyrrolidone - 20% --Epoxidized coconut oil
--1% 5% These solutions are suitable for application by spraying.

F5 Granule al b1 Compounds of Tables 1 to 9 5% 10% Kaolin 94% - Highly dispersed silicic acid 1% - Attapulgite - 90% The active ingredient is dissolved in methylene chloride, the solution is rtttm to the carrier, and then the solvent is evaporated under reduced pressure.

F4. Powder a) b1 Compounds in Tables 1 to 9 2% 5% Highly dispersed silicic acid 1% 5% Talc powder 97% - Chikaraolin - 90% Ready-to-use powder can be obtained by thoroughly mixing the active ingredient with a carrier, etc. It will be done.

Examples of formulations of solid active ingredients of formula I (total, percent) [by weight]. )p 5. Irrigation agent al bl
cJ Compounds in Tables 1 to 9 25% 50% 75% Sodium lignosulfonate 5% 5% - Sodium lauryl sulfate 3% -5% Sodium cyinobutylnaphthalene sulfonate -6% 10% Highly dispersed silicic acid 5% 10% 10% Kaolin 62% 27% - The active ingredient is thoroughly mixed with the adjuvants, and the mixture is thoroughly ground in a suitable grinder and diluted with water to obtain a suspension of the desired concentration. Irrigation agent can be obtained.

F6. Emulsion Concentrate Compounds of Tables 1 to 9 10% Calcium dodenlebenzenesulfonate 3% Cyclohexanone 50% Xylene mixture 50% An emulsion of the required concentration can be obtained from this concentrate by dilution with water. I can do it.

F7 powder a) b) Compounds of Tables 1 to 9 5% 8% Talc powder 95% - Kaolin - 92% Ready-to-use powders are prepared by mixing the active ingredient with the carrier and grinding the mixture in a suitable grinder. It is obtained by

Fa extruded granules Compounds of Tables 1 to 9 10% Sodium lignosulfonate 2% Carboxymethylcellulose 1% Cocoa 7 87% The active ingredient is mixed with the auxiliaries and ground and the mixture is subsequently moistened with water. The mixture is extruded and then dried in a stream of air.

F9. Coated Granules Compounds of Tables 1 to 9 3% Polyethylene Glycol 200 6% Cocoa 7 94% The finely ground active ingredient is applied evenly with a mixer to the kaolin moistened with polyethylene glycol. In this way, non-powdery coated granules are obtained.

Compounds of Tables 1 to 9 40% Ethylene glycol 10% Sodium lignosulfonate 10% Carboxymethyl cellulose 1% 67% formaldehyde in water 02% Silicone oil in the form of a 75% aqueous emulsion 08% Water 32% Finely ground active ingredients are A suspension concentrate is obtained which can be thoroughly mixed with auxiliaries and diluted with water to obtain a suspension of the desired concentration.

a) Residual protection effect Wheat plants were treated 6 days after sowing by spraying with a spray mixture prepared from a wettable powder mixture containing the active ingredient ((102%). Plants post-treated for 24 hours were treated with fungal summer The infected plants were infected with a spore suspension at a relative humidity of 95 to 10
0% and about 20°C for 48 hours and then placed in a greenhouse at about 22°C. Evaluation of the development of rust pus was performed on the 12th day after infection.

b) Active ingredient after 5 days of percolation sowing (α006% based on soil volume)
Wheat was treated with a spray mixture prepared from an irrigation formulation containing ). After 48 hours the treated plants were infected with a suspension of fungal diaspores.

The plants are then kept at a relative humidity of 95 to 100% and about 2
Incubation for 48 hours at 0°C11 and then placed in a greenhouse at approximately 22°C - evaluation of the development of rust pustules was carried out on the 12th day after infection.The compounds in the table were highly effective against rust fungi. Ta.

The rust fungus attack on untreated infected control plants was 100%. Compounds 1.1 to 1.4.1.1
9.1.49.1.51. i, 57°1.78.1.9
6.1.111.1.125.1151.1.178゜1.184.1.205.1.207.1, 210.1
,211°1.213. t214.1, 216, 12
1B, 1.220.2.1゜2.4.2.49.2.
51. Z96.2, 207.2, 208.2, 210
゜2.211.2.212.3.1.3.4.5.49
．． 3.51.5,206°4.1.4.24. &1.
7. i, 7.2. al, a2. a3. a28
゜9.1 Others suppressed the attack by rust fungi to 5%.

Residual protective effect on groundnut plants of 10 to 15 tyn height prepared from an irrigation formulation containing the compound to be tested [also spray mixture +0
．． 006%) and infected with a suspension of conidia of the fungus 48 hours later. Approximately 2 infected plants
It was incubated for 72 hours at 1° C. and high humidity and then placed in a greenhouse until the typical spots appeared on the leaves. Evaluation of bactericidal activity was carried out on the 12th day after infection and was based on the number and size of spots.

Untreated infected controls (number and size of spots - 100
%), the attack of Cercospora (Cerco-5 pora l fungi) on peanut plants treated with the compound was significantly reduced. In the above test, compound 1.1
or 1.4.19°149, 1.78.1.96.1
, 111.1, 125° 1.126.1, 151.1.
178.1, 184.1, 205゜1.206.1.2
07.1.213.1, 216.1.218゜1.22
0.2.1. 2.4. 2.49.2.51.2.9
6゜2.211.2, 212.2. f, 2.4.3.4
9.3.51°! 1,207.4. L 4.2'4.
&1.7.1.7.2.8.1. a3゜a2B and 9
No. 1 almost completely suppressed the occurrence of spots (to 10%).

a) Residual Protection Barley plants approximately 8 m high are sprayed with a spray mixture (10.002%) prepared from the active ingredients formulated as a hydrating agent. The treated plants are sprinkled with fungal conidia after 3 to 4 hours. The infected barley plants were then heated to approximately 22°C.
Place it in a greenhouse.

The degree of spread of the bacteria is evaluated after 10 days.

b) Osmosis Barley plants approximately 87 m high are treated with a spray mixture (0.002% based on the soil volume) prepared from the compound to be tested formulated as a hydrating agent. Care must be taken to avoid contact of the spray mixture with growing parts of plants.

The treated plants are infected after 48 hours with a suspension of fungal conidia. The infected barley plants are then placed in a greenhouse at approximately 22° C. and an assessment of the spread of the fungus is made after 10 days.

The compound represented by formula 1 is Ery-5i
phe) is very effective against bacteria. Erysiphe I fungal attack was 100% against untreated infected control plants. Individual compounds in the table inhibited fungal attack in barley by less than 30%.

Example B4: Venturia 1naequalis (Venturia 1naequalis) in apple dressing
A mist mixture (0,006%) prepared from a hydrated formulation containing the compound to be tested was sprayed. the plant 2
After 4 hours, the cells were infected with a suspension of fungal conidia. The plants were then kept at relative humidity for 5 days. The cells were cultured at 100% capacity and kept in a greenhouse at 20-24°C for an additional 10 days. Spread of spot disease was evaluated on day 15 post-infection. Compounds in the table, e.g. compounds 1.1, 1.51.1, 126.1
．． 127.1.17B.

1.184.1, 205.1, 206.1, 210.1
．． 211°1215, 1,217.1,218.14.
2-51.2.96゜2.207. 2,208. 2
．． 210. 2.211. ．． 3.1. 3.4°! L
205.5.206.4.1.4.24.6, 1.71
7.8.1 and a2 suppressed the attack to less than 25%. On the other hand, the attack on untreated infected controls was 10
I was in charge 0.

Example B5: Botrytis cinerea in beans (Botr
ytis cinerea) Bean plants at a height of 10,000 ml were sprayed with a spray mixture (002% concentration) prepared from an irrigation formulation of the compound to be tested.

After 48 hours, the treated plants were infected with a suspension of fungal conidia. The infected plants were incubated for 3 days at 95-100% relative humidity and 21°C and then evaluated for fungal attack. Many of the compounds in the table very strongly inhibited fungal infections. Compound 1.1 Insulator 1.4.1.49゜1
．． 51.1.57.1.196.1.1B4.1,21
Concentrations of 0.1211 and 2.4iin02% were fully effective (oral or 8% attack). The attack of G. spp. on untreated infected bean plants was 10.
After 3 weeks of cultivation, the tomato plants were sprayed with a spray mixture (a06%) prepared from the water preparation containing the compound to be tested. After 24 hours, the treated plants were infected with a suspension of fungal sporangia. After culturing the plants for 5 days at 90-100% relative humidity and 20° C., fungal attack was evaluated.

I)) A systemic spray mixture (0.06 cycles based on the volume of soil) was prepared from the irrigation mix containing the compound to be tested and applied to the tomato plants after 1.6 weeks of cultivation.

(Be careful not to let the fog mixture come into contact with growing parts of the plants. After 48 hours, infect the plants with a suspension of fungal sporangia.
% and fungal attack after 5 days of incubation at 20°C +i11+.

In the above test, compounds 1.1 to 14°1.1
? , 1.49.1.51.1.57.1.78.1.
96. tllll.

1.125, 1.151, 1.178, 1.184, 1
205゜1.207.1.210.1, 211.1.2
13.1214.1,216゜1.218.1,220
．． 2.1.2.4.2. ．． 49. Z5f, 2.96
゜2.207.2.208.2, 210.2.211.
2.212.3. j.

3.4.5.49.3.51. 5206.4.1.4.
24.6.1.7.1゜7.2. al, a2. B
, 3. a2B, 9.1 and others had very good penetration effect. These compounds inhibited fungal attack almost completely VL (0 to 5% attack) compared to 100% attack in untreated control plants.

a) Residual protection effect Spraying mixture (a06
%) was sprayed. After 24 hours, the treated plants are infected with a suspension of fungal sporangia. Relative humidity 95 to 100
% and fungal attack after 6 days of incubation at 20°C.

b) Residual therapeutic effect Cuttings of vines at the 4- to 5-leaf stage were infected with a prespore suspension of the fungus. 2 in humidchamber I at 95-100% relative humidity and 20°C.
After 4 hours of incubation, the infected plants were dried and sprayed with a spray mixture prepared from the water preparation containing the compound to be tested (2).
(106%) was sprayed. 1. After drying the new cover, place the treated plants in a humid chamber.
I returned it to . Evaluation of fungal attack was performed on the 6th day after female infection.

The compounds of Tables 1 to 8 are used in the production of Plasmopara viticola in grape vines.
) showed very good bactericidal activity. For example, compounds 1.1, 1.2, 1.3 and 1.4 completely inhibited fungal attack (~5%).

Residual therapeutic effect 2? After intercultivation, the rice plants were sprayed with a spray mixture (002%) prepared from the hydrated 02 mixture containing the compound to be tested. 48 hours post-treated plants were infected with a suspension of fungal conidia. After 5 days of incubation at 95-100% relative humidity and 24° C., fungal attack was evaluated.

Compound 1.1.1.2.1.3.1.51°+, compared to 100% attack in untreated control plants.
96.1, 205.2.4. Fungal attack was less than 10% in rice plants treated with one of 551 and 81.

Claims (1)

[Claims] +11 General formula ■: [In the formula, R and R2 independently represent a NO2 group or a CF3 group, or one of R and R represents a hydrogen atom, and R8 represents a hydrogen atom an atom or a halogen atom, R4 is a hydrogen atom or a -C(0)R' group (in the group, R' is unsubstituted or a halogen atom, an alkoxy group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms). represents an alkyl group having 1 to 4 carbon atoms substituted by an alkylthio group, and R6, R6 and R7 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a thiocyan7 group, a mercapto group. group, alkyl group having 1 to 6 carbon atoms, L 6 F) having 1 carbon atom) /-roalkyl group, having 1 carbon atom
an alkoxy group of 1 to 6 carbon atoms, a nitro group, a cyano group, an alkoxy group of 1 to 5 carbon atoms, an alkylthio group of 1 to 3 carbon atoms, and/or ) C 1 -C 6 alkoxy substituted by C 3 -C 6 cycloalkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkoxy; Alkynyloxy group, number of carbon atoms: 1
alkylthio group having 5 to 6 carbon atoms, alkenylthio group having 5 to 6 carbon atoms, alkylsulfonyl group having 1 to 6 carbon atoms, alkylsulfoxyl group having 1 to 60 carbon atoms, alkenyl group having 3 to 6 carbon atoms, carbon Haloalkenyl group having 3 to 6 atoms, alkynyl group having 3 to 6 carbon atoms, haloalkynyl group having 3 to 6 carbon atoms or N (alkyl having 1 to 4 carbon atoms) 2
represents a group, and R5 is further unsubstituted or a halogen atom, a nitro group,
Cyano group, C1-C4 alkyl group, C1-C30 alkyl group, 2 N-(C1-C3 alkyl) groups and/or C1-C3 alkyl group
1 to 3 selected from fx, 3 alkoxy groups
It may also be a phenyl or benzyl group substituted by several identical or different groups. ] A compound represented by (2) In the above formula 1, R1 represents a No2 group or a CF group, and R2 represents a No2
or CF3 group, R3 represents a hydrogen atom or a halogen atom, and R4 represents a hydrogen atom or -C(QIR
' group (in the group, R' is unsubstituted or) - a C1-C4 alkyl group substituted with a rogen atom, a C1-C3 alkoxy group, or a C1-C3 alkylthio group; ), and R5, R6, and R7 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a thiocyano group, a mercapto group, an alkyl group having 1 to 6 carbon atoms, or 1 to 60 carbon atoms. haloalkyl, C1 -C6 alkoxy or N-, nitro, cyanogen, C1 -C6 alkoxy, C1 -C6 alkylthio and/or N- represents a C1-C6 alkoxy group substituted by C1-C4 alkyl), or a C3-C6 cycloalkoxy group, a C5-C6 alkenyloxy group; group, number of carbon atoms: 3
from 1 to 6 alkynyloxy groups, from 1 to 6 carbon atoms
alkylthio group, C3-C6 alkenylthio group, C1-C6 alkylsulfonyl group, C1-C6 alkylsulfoxyl group or N(C1-C4 alkyl)2 represents a group, and R5 is further unsubstituted, or a halogen atom, a nitro group, a cyano group, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms,
1 selected from 2 N (alkyl having 1 to 60 carbon atoms) and/or alkoxy group having 1 to 5 carbon atoms;
The compound according to claim 1, which may be a phenyl or benzyl group substituted by 1 to 3 identical or different groups. (3) In the above formula I, R represents a nitro group, R2 represents a trifluoromethyl group, R3 represents a chlorine atom, and R4 represents a hydrogen atom or 1C(0)-R' (in the group,
R' represents an alkyl group having 1 to 4 carbon atoms which is unsubstituted or substituted with a halogen atom, an alkoxy group having 1 to 3 carbon atoms, or an alkylthio group having 1 to 5 carbon atoms. ), and R5 is a hydrogen atom, a rogen atom, a cyano group, a thiocyano group, an alkyl group having 1 to 6 carbon atoms, a roalkyl group having 1 to 3 carbon atoms, and 1 to 6 carbon atoms.
0 alkoxy group, C1 -C60 alkoxy group, C1 -C3 alkylthio- (C1 -C3 alkoxy) group, C1 -C5 alkylthio group, N (carbon alkyl having 1 to 2 atoms) substituted with 2 groups having 1 to 3 carbon atoms
represents an alkoxy group having 3 to 4 carbon atoms, or an alkenyloxy group having 3 to 4 carbon atoms, an alkenylthio group having 3 to 4 carbon atoms, an alkylsulfonyl group having 1 to 5 carbon atoms, an alkylsulfonyl group having 1 to 3 carbon atoms; xyl group, N (alkyl having 1 to 6 carbon atoms) 2 groups or unsubstituted or fluorine atom, chlorine atom, bromine atom, 2) C
phenyl or benzyl substituted with 1 to 3 groups of the same size and different size selected from 7 groups, cyan groups, methoxy groups, alkyl groups having 1 to 4 carbon atoms, dimethylamino groups, or CF3 groups; represents a group, and R
6 and R7 are each independently a hydrogen atom, a hydrogen atom, a cyan group, a thiocyano group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. or a carbon atom substituted by a halogen atom, a nitro group, an alkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 3 carbon atoms, or 2 N (alkyl having 1 to 4 carbon atoms) groups. Represents an alkoxy group of 1 to 6 carbon atoms, an alkylthio group of 1 to 4 carbon atoms, an alkylsulfonyl group of 1 to 3 carbon atoms, an alkylsulfoxyl group of 1 to 3 carbon atoms, 3 carbon atoms C6-4 alkenyloxy, C6-4 alkenylthio, C6-4 alkynyloxy, C6-4 alkynylthio or N (C1-C3 alkyl) ) 2 groups according to claim 2. (4) The compound according to claim 6, wherein in the formula I, R4 represents a hydrogen atom, and the other substituents have the meanings described in claim 3. (5) In the above formula I, R1 represents a nitro group, R2 represents a trifluoromethyl group, R3 represents a hydrogen atom, and R4 represents a hydrogen atom or a -C(OIR' group (in which R' is an unrepresented represents a C1-C4 alkyl group substituted with a halogen atom, a C1-C3 alkoxy group, or a C1-C3 alkylthio group), and R is a hydrogen atom; -rogen atom, cyano group, thiocyano group, alkyl group having 1 to 6 carbon atoms, no-roalkyl group having 1 to 3 carbon atoms, 1 to 6 carbon atoms
alkoxy group, C1 -C6 no-roalkoxy group, C1 -C60 alkylthio- (C1 -C6 alkoxy) group, C1 -C3 alkylthio group, N-( a C1-C3 alkoxy group substituted by C1-C2 alkyl), a C3-C40 alkenyloxy group, a C3-C4 alkenylthio group, Alkylsulfonyl group having 1 to 6 carbon atoms, alkylsulfoxyl group having 1 to 6 carbon atoms, 2 N (alkyl having 1 to 3 carbon atoms) or unsubstituted or fluorine atom, chlorine atom, bromine atom , a phenyl or benzyl group substituted with 1 to 3 same or different groups selected from a nitro group, a cyano group, a methoxy group, a C1-C4 alkyl group, a dimethylamino group or a CF3 group; , and R6 and R7 are each independently a hydrogen atom, a -rogen atom, a cyano group, a thiocyano group, an alkyl group having 1 to 3 carbon atoms, a -roalkyl group having 1 to 3 carbon atoms, and 1 carbon atom. An alkoxy group or No.1
0 Ken atoms, nitro groups, C1 -C3 alkoxy groups, C1 -C3 alkylthio groups or C1 -C6 atom substituted by 2 N (C1 -C4 alkyl) groups represents an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, an alkylsulfonyl group having 1 to 3 carbon atoms, an alkylsulfoxyl group having 1 to 3 carbon atoms, or an alkylthio group having 1 to 4 carbon atoms;
-4 alkenyloxy group, having 5 -4 carbon atoms
an alkenylthio group having 3 to 4 carbon atoms, an alkynyloxy group having 3 to 4 carbon atoms, an alkynylthio group having 3 to 4 carbon atoms or 2 groups of N (alkyl having 1 to 3 carbon atoms) according to claim 2 Compound. (6) A compound according to claim 5, wherein in formula I, R4 represents a hydrogen atom, and the other substituents have the meanings specified in claim 5. (7) In the above formula I, R1 represents a trifluoromethyl group, R2 represents a nitro group, R3 represents a hydrogen atom, and R4 represents a hydrogen atom or a -C(0)R' group (in the group, R' represents an alkyl group having 1 to 4 carbon atoms which is unsubstituted or substituted with a halogen atom, an alkoxy group having 1 to 3 carbon atoms, or an alkylthio group having 1 to 5 carbon atoms, and R5 is a hydrogen atom; , halogen atom, cyano group, thiocyano group, alkyl group having 1 to 6 carbon atoms, 1 carbon atom
haloalkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 6 carbon atoms, haloalkoxy group having 1 to 3 carbon atoms, alkylthio-(alkoxy having 1 to 3 carbon atoms) group having 1 to 3 carbon atoms, carbon Number of atoms: 1 to 3
an alkylthio group, or N (having 1 to 2 carbon atoms)
C1-C6 alkoxy substituted by C3-C4 alkyl), C3-C4 alkenyloxy, C3-C4 alkenylthio, C1-C4 alkenylthio; 3 alkylsulfonyl group, Fi [i 1 to 5 alkylsulfoxyl group, 2 N (alkyl having 1 to 3 carbon atoms), or unsubstituted or fluorine atom, chlorine atom, bromine atom, nitro group, R6 and R7 is independently a hydrogen atom, a halogen atom, a cyano group, a thiocyano group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or carbon Alkylthio group having 1 to 6 atoms or N (having 1 carbon atom
C1-C3 alkoxy substituted by C1-C4 alkyl), C1-C4 noalkylthio, C1-C50 alkylsulfonyl, C1-C3 fi1-3; an alkylsulfoxyl group having 3 to 4 carbon atoms, an alkenyloxy group having 3 to 4 carbon atoms, an alkenylthio group having 5 to 4 carbon atoms, an alkynyloxy group having 5 to 4 carbon atoms, an alkynylthio group having 3 to 4 carbon atoms or 3. A compound according to claim 2, which represents two groups iN (alkyl having 1 to 3 carbon atoms). (8) The compound according to claim 7, wherein in the formula (1), R4 represents a hydrogen atom, and the other substituents have the meanings described in claim 7. (9) The compound represented by the above formula
-Medoxyvirimidine (compound 1.1), N-(3'-chloro-2', b'-dinitro-4'-
trifluoromethylphenyl)-5-amino-4,6-
dimethylthiopyrimidine (compound 1.2), N-(5'
-chloro-2', Is'-7 nitro-4'-trifluoromethylphenyl)-5-amino-4,6-dydolyfluoroethoxypyrimidine (compound 1.5), N-(5'-chloro-), 6'-dinitro-4'-trifluoromethylphenyl)-5-amino-4,6-dichloropyrimidine (compound 1.4), Nt3'-chloro-7,6'-dinitro-4'-trifluoro methylphenyl)-5-amino-4-chloro-6-methylmercaptopyrimidine (compound 1.1841, N-(5'-chloro-27,6/-dinitro-4'-trifluoromethylphenyl)-5-amino -4-riar
y-2-methyl-6-methylpyrimidine (compound t20
5), N-(3-chloro-2-6'-dinito-4'-)lifluoromethylphenyl)-5-aminol 2-chloro-4
-methoxypyrimidine (compound 1.511, N-+3'-chloro-2/, 6/-dinitro-4'-
trifluoromethylphenyl)-5-amino-2,4-
Dichloropyrimidine (compound 1.49), N-(3'-
Chloro-2', 6'-dinitro-4'-trifluoromethylphenyl)-5-amino-2-chloro-4-allyloxypyrimidine (compound 1.210), N-(3'-chloro-2', 6'-dinitro-4'-trifluoromethylphenyl)-5-amino-2-chloro-4-allylmercaptopyrimidine (compound 1.57)
, N-(3'-chloro-2', 6L-dinitro-4'-
trifluoromethylphenyl)-5-amino-2-trio
a-4-phrovargyloxypyrimidine (compound 1゜211), N −+ 5'-chloro-2', 6'-dinitro-4'
-trifluoromethylphenyl)-5-amine4.6-
Dichloro-2-methylpyrimidine (compound 1.96), N-(5'-chloro-2-6'-dinitro-47-trifluoromethylphenyl)-5-amino-4,6-dichloro-2-phenylpyrimidine (Compound 1.1251, N-(2',6'-dinitro-4'-trifluoromethylphenyl)-5-amino-4,6-dichloropyrimidine (Compound 2.4+, N-(2',4'-dinitro-6'-trifluoromethylphenyl)-5-amino-4,6-dicaropyrimidine (compound i 4 J. N-(2', 4', 6'-)IJ=)rophenyl J
-s-amino-4,6-dichloropyrimidine (compound 7
．． 1), the compound according to claim 1 selected from the group consisting of N - (2'-nitro-4'-trifluoromethylphenyl)-5-amino-4,6-dichloropyrimidine (compound a1) . (II The following formula ■: f (wherein R1 and R2 independently represent NO, a group or a CF3 group, or one of R and R2 represents a hydrogen atom, and R3 is a hydrogen atom or a halogen atom and Hal represents a halogen atom. group, thiocyano group, mercapto group, C1-C6 alkyl group, C1-C6 haloalkyl group, C1-6 alkoxy group, or halogen atom, nitro group, cyano group, carbon atom C1-C6 alkoxy group, C1-C5 alkylthio group and/or FiN (C1-C6 alkoxy group substituted by C1-C4 alkyl h group); A cycloalkoxy group having 3 to 3 carbon atoms, a γlganyloxo group having 5 to 6 carbon atoms, an alkynyloxy group having 3 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, and a cycloalkoxy group having 6 to 6 carbon atoms. alkenylthio7, C1-C6 alkylsulfonyl group, C1-C6 alkylsulfoxyl group, C3-C6 alkenyl group, C3-C6 alkenyl group
represents a haloalkenyl group, an alkynyl group having 5 to 6 carbon atoms, a haloalkynyl group having 3 to 6 carbon atoms, and 2 groups (alkyl having 1 to 4 carbon atoms),
And R5 is further unsubstituted or a halogen atom, a nitro group, a cyan group, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, or 2 N-(alkyl having 1 to 3 carbon atoms) groups. and/or a phenyl or benzyl group substituted with 1 to 5 same or different groups selected from alkoxy groups having 1 to 3 carbon atoms. ) in the presence of a base to form a compound represented by the following formula 1" R, R7 (wherein R1, R2, R3, R5, R6 and R7 have the above meanings). A compound represented by the formula 1' is N-acylated with a reactive derivative of a carboxylic acid represented by the following formula: General formula 1゜ (in the formula, R4 is a hydrogen atom or -C(OIR' group (in the group, R' is an unsubstituted or halogen atom, an alkoxy group having 1 to 3 carbon atoms) to obtain an acylated derivative; or a C1-C4 alkyl group substituted by a C1-C6 alkylthio group), and RI% R2, R3, R5, R6 and R7 have the above meanings.1 A method for producing a compound represented by: OD General device [wherein R1 and R2 independently represent a No2 group or a CF3 group, or one of R1 and R2 represents a hydrogen atom, and R3 is a hydrogen atom or a halogen R4 represents a hydrogen atom or -C(01R' group (in the group, R' is unsubstituted or substituted with a halogen atom, an alkoxy group having 1 to 3 carbon atoms, or an alkylthio group having 1 to 3 carbon atoms); represents an alkyl group having 1 to 4 carbon atoms), and Rs, R6 and R7 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyan group, a thiocyano group, a mercapto group, or a mercapto group having 1 to 4 carbon atoms. 6 alkyl group, C 1 -C 6 alkyl group, C 1 -C 6 alkyl group, C 1 -C 6 alkyl group
by an alkoxy group, or a halogen atom, a nitro group, a cyan group, an alkoxy group having 1 to 3 carbon atoms, an alkylthio group having 1 to 3 carbon atoms, and/or 2 groups of N (alkyl having 1 to 4 carbon atoms) It represents a substituted alkoxy group having 1 to 6 carbon atoms, or alternatively a cycloalkoxy group having 3 to 6 carbon atoms, an alkenyloxy group having 3 to 6 carbon atoms, or an alkynyloxy group having 3 to 6 carbon atoms. group, an alkylthio group having 1 to 6 carbon atoms, an alkenylthio group having 3 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms,
C1-C6 alkylsulfoxyl, C5-6 alkenyl, C3-6 haloalkenyl, C3-6 alkynyl, C3-6 represents a haloalkynyl group or 2 N (alkyl groups having 1 to 4 carbon atoms), and R5 is further unsubstituted or a halogen atom, a nido group, a cyan group, an alkyl group having 1 to 4 carbon atoms, substituted with 1 to 3 same or different groups selected from 1 to 6 haloalkyl groups, 2 N-(C 1 to 3 alkyl) groups, and/or C 1 to 3 alkoxy groups; It may also be a phenyl or benzyl group. A composition for controlling or preventing attack by pests, which contains at least one of the compounds represented by the following formula, in combination with customary auxiliaries and carriers. θλ is applied to a cultivated plant or its cultivation area in an effective amount,
To control plant pathogenic pests